
Discover tips and strategies to find the most affordable flight options for your journey from Tulsa (TUL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (Southwest) |
One-way from | $160 (American Airlines) |
Popular in | July |
Cheapest in | October |
Average price | $364 |
Good round-trip deal | $322 or less |
Good one-way deal | $200 or less |
Fly from
Fly to
Route
Depart
Return
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Tue 12/8
3:05 pm-5:00 pm
Nonstop1h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Wed 12/9
6:00 am-4:17 pm
2 stops10h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Tue 12/8
7:30 am-2:12 pm
1 stop6h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Tue 12/8
6:58 pm-11:56 pm
1 stop4h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Tue 12/8
6:00 am-4:50 pm
2 stops10h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Thu 1/21
5:35 am-7:20 am
Nonstop1h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Fri 12/25
4:08 pm-10:05 pm
1 stop5h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Fri 12/18
6:58 pm-11:56 pm
1 stop4h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Fri 12/25
11:00 am-8:18 pm
2 stops9h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Tue 5/11
12:36 pm-8:37 pm
2 stops8h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
Everything you need to know about your flight from Tulsa to Chicago
Food
Crew
Boarding
Comfort
Overall
Entertainment
Reviews
Reza,Jun 2026
TPA - MDW
Food
Crew
Boarding
Comfort
Overall
Entertainment
Reviews
Reza,Jun 2026
TPA - MDW
Food
Crew
Boarding
Comfort
Overall
Entertainment
Reviews
Reza,Jun 2026
TPA - MDW
Food
Crew
Boarding
Comfort
Overall
Entertainment
Reviews
Reza,Jun 2026
TPA - MDW
Find useful and relevant information for your journey from Tulsa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$398 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$381 | FlexibilityNo cancel fee | On-time63% |