$100+ Cheap flights from Chicago (CHI) to Pueblo, CO
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Pueblo with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Pueblo are usually found in October or September, booked 85 days in advance, depart on a Saturday or Wednesday and return on a Friday
Cheap flight deals from Chicago to Pueblo
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Best
Last-minute
One-way
Cheapest flights from Chicago to PuebloExplore the most affordable flight options available from Chicago to Pueblo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
Explore the most affordable flight options available from Chicago to Pueblo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Mon 10/196:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Deal found 6/8![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Tue 10/276:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Deal found 6/4![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Wed 9/210:00 am
DEN
- ORD
1 stop8h 55m
Frontier
Deal found 6/4![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/249:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Fri 7/315:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/8![Frontier logo]()
$174
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Thu 8/69:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/8![United Airlines logo]()
$175
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Sat 7/115:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/8![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Tue 9/85:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/7![Frontier logo]()
$177
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Sun 9/65:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/7![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/249:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Mon 6/295:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/4![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/29:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Tue 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/4![Frontier logo]()
$180
This Super.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Wed 7/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/8![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Wed 8/266:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$183
Best flights from Chicago to PuebloDiscover carefully curated flight deals from Chicago to Pueblo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
Discover carefully curated flight deals from Chicago to Pueblo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:40 pm
ORD
- DEN
1 stop4h 19m
Delta
Tue 10/206:10 am
DEN
- ORD
1 stop4h 32m
Delta
Deal found 6/8![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:55 am
MDW
- DEN
1 stop5h 00m
Southwest
Sun 8/96:10 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/8![Southwest logo]()
$218
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Wed 10/146:10 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Deal found 6/8![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am
ORD
- DEN
1 stop7h 03m
Delta
Mon 11/1610:30 am
DEN
- ORD
1 stop7h 10m
Delta
Deal found 6/8![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:30 am
MDW
- DEN
Nonstop2h 30m
Southwest
Wed 8/1211:15 am
DEN
- MDW
1 stop4h 45m
Southwest
Deal found 6/8![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:45 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Mon 9/287:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:20 pm
ORD
- DEN
1 stop6h 28m
Delta
Wed 8/196:05 am
DEN
- ORD
1 stop6h 08m
Delta
Deal found 6/5![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Wed 7/89:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/8![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Tue 8/1811:15 am
DEN
- MDW
1 stop4h 45m
Southwest
Deal found 6/5![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1111:30 am
ORD
- DEN
1 stop7h 00m
Delta
Thu 10/156:45 am
DEN
- ORD
1 stop4h 52m
Delta
Deal found 6/8![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:25 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Tue 7/146:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/8![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:20 pm
ORD
- DEN
1 stop6h 39m
Delta
Fri 10/166:45 am
DEN
- ORD
1 stop4h 52m
Delta
Deal found 6/4![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:05 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Sat 7/188:20 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/8![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:18 pm
ORD
- DEN
1 stop6h 26m
Delta
Sat 8/16:05 am
DEN
- ORD
1 stop6h 41m
Delta
Deal found 6/7![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/289:05 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Sun 8/28:55 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/6![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:17 am
ORD
- DEN
1 stop6h 55m
Delta
Sun 9/206:05 am
DEN
- ORD
1 stop5h 59m
Delta
Deal found 6/7![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:25 am
MDW
- DEN
1 stop4h 10m
Southwest
Sun 8/166:10 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/5![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:13 pm
MDW
- DEN
1 stop5h 12m
Delta
Sun 9/276:00 am
DEN
- MDW
1 stop6h 07m
Delta
Deal found 6/8![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:45 pm
MDW
- DEN
1 stop4h 50m
Southwest
Thu 11/128:40 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:25 pm
MDW
- DEN
1 stop5h 09m
Delta
Tue 8/186:00 am
DEN
- MDW
1 stop6h 10m
Delta
Deal found 6/7![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:00 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Tue 7/76:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/6![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 pm
ORD
- DEN
1 stop6h 39m
Delta
Sun 10/256:45 am
DEN
- ORD
1 stop4h 52m
Delta
Deal found 6/5![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:18 pm
ORD
- DEN
1 stop6h 26m
Delta
Sat 8/16:05 am
DEN
- ORD
1 stop6h 41m
Delta
Deal found 6/6![Delta logo]()
$285
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:57 pm
ORD
- DEN
1 stop6h 37m
Delta
Tue 9/86:45 am
DEN
- ORD
1 stop4h 54m
Delta
Deal found 6/4![Delta logo]()
$301
Last-minute flights from Chicago to PuebloDiscover last-minute flight deals from Chicago to Pueblo. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Pueblo. Data last updated June 9, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Tue 6/305:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/7![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/249:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Mon 6/295:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/4![Frontier logo]()
$179
This Super.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Sat 7/45:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/8![Frontier logo]()
$183
This Super.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Tue 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/8![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/29:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Tue 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/4![Frontier logo]()
$180
This Super.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Sat 7/115:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/5![Frontier logo]()
$173
This Super.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Wed 7/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/8![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Thu 7/165:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/4![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Sat 7/115:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/8![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/249:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Fri 7/315:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/8![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Wed 8/56:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Mon 8/35:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/7![Frontier logo]()
$178
One-way flights from Chicago to PuebloSearch for one-way flight options from Chicago to Pueblo. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
Search for one-way flight options from Chicago to Pueblo. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/7![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:50 pm
ORD
- DEN
1 stop25h 11m
Frontier
Deal found 6/4![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:04 pm
MDW
- DEN
1 stop11h 12m
Frontier
Deal found 6/4![Frontier logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/8![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:45 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/7![Southwest logo]()
$104
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/7![Frontier logo]()
$108
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:50 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Deal found 6/4![United Airlines logo]()
$109
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 6/4![Southwest logo]()
$109
This Super.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/5![Frontier logo]()
$111
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:25 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/8![Southwest logo]()
$111
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- DEN
1 stop8h 04m
Frontier
Deal found 6/4![Frontier logo]()
$113
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:25 pm
MDW
- DEN
1 stop5h 09m
Delta
Deal found 6/8![Delta logo]()
$113
Find flight deals from Chicago to Pueblo
Keep the following information in mind while searching for Chicago to Pueblo flight deals. Data was last updated June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (Frontier) |
One-way from | $100 (Cheapflightsfares) |
Popular in | March |
Cheapest in | October |
Average price | $271 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Pueblo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 9, 2026.
Use the filters below to find and compare flights from Chicago to Pueblo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Tue 10/13
7:40 pm-10:59 pm
1 stop4h 19m
Denver Intl
Tue 10/20
6:10 am-11:42 am
1 stop4h 32m
$197
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Tue 11/10
6:00 am-12:03 pm
1 stop7h 03m
Denver Intl
Mon 11/16
10:30 am-6:40 pm
1 stop7h 10m
$211
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 8/5
8:55 am-12:55 pm
1 stop5h 00m
Denver Intl
Sun 8/9
6:10 am-9:35 am
Nonstop2h 25m
$218
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Sun 8/9
6:30 am-8:00 am
Nonstop2h 30m
Denver Intl
Wed 8/12
11:15 am-5:00 pm
1 stop4h 45m
$218
Quickest round-trip
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 9/25
8:45 pm-10:20 pm
Nonstop2h 35m
Denver Intl
Mon 9/28
7:00 am-10:20 am
Nonstop2h 20m
$224
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 8/12
1:55 pm-7:50 pm
2 stops6h 55m
Denver Intl
Tue 8/18
11:15 am-5:00 pm
1 stop4h 45m
$233
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Wed 10/14
5:00 am-6:39 am
Nonstop2h 39m
Denver Intl
Wed 10/14
6:10 pm-9:52 pm
Nonstop2h 42m
$239
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 7/10
9:25 pm-11:10 pm
Nonstop2h 45m
Denver Intl
Tue 7/14
6:15 am-9:40 am
Nonstop2h 25m
$241
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Wed 8/12
5:20 pm-10:48 pm
1 stop6h 28m
Denver Intl
Wed 8/19
6:05 am-1:13 pm
1 stop6h 08m
$247
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 7/15
9:05 pm-10:55 pm
Nonstop2h 50m
Denver Intl
Sat 7/18
8:20 pm-11:45 pm
Nonstop2h 25m
$251
Showing 1-10 of 46 resultsSorted by cheapest first
Best time to book a flight from Chicago to Pueblo
Have a flexible travel schedule? Discover the best time to fly to Pueblo from Chicago with our price prediction graph.
ORD-DEN
MDW-DEN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Pueblo
CHI-PU5
ORD-DEN
MDW-DEN
What is the cheapest time of day to fly from CHI to PU5?
Find hourly flight availability from Chicago to Pueblo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 9, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 24% on flights from Chicago to Pueblo by exploring options for tickets in the afternoon.
Weekly flight availability from Chicago to Pueblo
Explore weekly flight availability from Chicago to Pueblo. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 9, 2026.
The most flights from CHI to PU5 are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Chicago to Pueblo?
Reviews of airlines servicing Pueblo
Get insights into the airlines that provide service to Pueblo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pueblo. Reviews last updated June 9, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Pueblo have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Pueblo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Find flights from Chicago to Pueblo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Pueblo flights
Browse other Chicago and Pueblo flight options. Last updated on June 9, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Pueblo
Discover the top 3 airlines that operate flights from Chicago to Pueblo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$191 | Average$321 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$239 | Average$453 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$246 | Average$379 | FlexibilityNo cancel fee | On-time69% |