We compare the same destinations and seven-night travel dates across ORD and MDW. This is the price spread in our actual samples—not a claim that one airport is always cheapest.
matched searches with a lowest fare
(including ties)
matched searches with a lowest fare
(including ties)
1180 matched date comparisons across 98 destinations. Both airport checks must be within 24 hours of each other.
The largest observed matched gap per destination. Open a route to see its dates and flight details.
| Destination / dates | ORD | MDW | Sampled gap |
|---|---|---|---|
| Dayton Dec 28–Jan 4 | $289 | $1,681 | $1,392ORD lowest, ties possible |
| Madison Dec 28–Jan 4 | $289 | $1,568 | $1,279ORD lowest, ties possible |
| Punta Cana Jun 27–Jul 4 | $549 | $1,701 | $1,152ORD lowest, ties possible |
| San Juan Jul 23–Jul 30 | $381 | $1,443 | $1,062ORD lowest, ties possible |
| Milwaukee Jun 27–Jul 4 | $249 | $1,203 | $954ORD lowest, ties possible |
| Munich Oct 11–Oct 18 | $1,010 | $1,963 | $953ORD lowest, ties possible |
| Istanbul Oct 11–Oct 18 | $1,063 | $1,990 | $927ORD lowest, ties possible |
| Frankfurt Oct 11–Oct 18 | $1,088 | $1,979 | $891ORD lowest, ties possible |
| Honolulu Jun 27–Jul 4 | $780 | $1,659 | $879ORD lowest, ties possible |
| Vancouver Dec 28–Jan 4 | $538 | $1,379 | $841ORD lowest, ties possible |
| Zurich Jul 23–Jul 30 | $939 | $1,762 | $823ORD lowest, ties possible |
| Amsterdam Jul 23–Jul 30 | $1,007 | $1,717 | $710ORD lowest, ties possible |
| Cancun Oct 11–Oct 18 | $568 | $1,253 | $685ORD lowest, ties possible |
| Tokyo Mar 15–Mar 22 | $1,135 | $1,738 | $603ORD lowest, ties possible |
| Burlington Oct 11–Oct 18 | $478 | $1,069 | $591ORD lowest, ties possible |
| Springfield Oct 11–Oct 18 | $314 | $893 | $579ORD lowest, ties possible |
| Fargo Nov 6–Nov 13 | $240 | $753 | $513ORD lowest, ties possible |
| Sioux Falls Nov 6–Nov 13 | $299 | $804 | $505ORD lowest, ties possible |
| Guadalajara Jun 27–Jul 4 | $499 | $988 | $489ORD lowest, ties possible |
| Appleton Oct 11–Oct 18 | $304 | $788 | $484ORD lowest, ties possible |
| Fayetteville Oct 11–Oct 18 | $299 | $764 | $465ORD lowest, ties possible |
| Madrid Jul 23–Jul 30 | $706 | $1,169 | $463ORD lowest, ties possible |
| Cedar Rapids Oct 11–Oct 18 | $368 | $814 | $446ORD lowest, ties possible |
| Lexington Oct 11–Oct 18 | $329 | $754 | $425ORD lowest, ties possible |
| Rome Jun 27–Jul 4 | $887 | $1,311 | $424ORD lowest, ties possible |
| Dublin Oct 11–Oct 18 | $827 | $1,219 | $392ORD lowest, ties possible |
| Sacramento Jun 27–Jul 4 | $427 | $818 | $391ORD lowest, ties possible |
| Traverse City Oct 11–Oct 18 | $304 | $674 | $370ORD lowest, ties possible |
| Paris Dec 28–Jan 4 | $988 | $1,347 | $359ORD lowest, ties possible |
| Denver Jun 27–Jul 4 | $316 | $672 | $356ORD lowest, ties possible |
| London Jun 27–Jul 4 | $1,026 | $1,370 | $344ORD lowest, ties possible |
| Green Bay Oct 11–Oct 18 | $304 | $644 | $340ORD lowest, ties possible |
| Mexico City Oct 11–Oct 18 | $376 | $712 | $336ORD lowest, ties possible |
| Phoenix Jun 27–Jul 4 | $367 | $698 | $331ORD lowest, ties possible |
| Fort Wayne Nov 6–Nov 13 | $289 | $619 | $330ORD lowest, ties possible |
| Syracuse Jul 23–Jul 30 | $319 | $648 | $329ORD lowest, ties possible |
| Seattle Jun 27–Jul 4 | $449 | $767 | $318ORD lowest, ties possible |
| Salt Lake City Jun 27–Jul 4 | $515 | $808 | $293ORD lowest, ties possible |
| Montreal Jan 23–Jan 30 | $378 | $654 | $276ORD lowest, ties possible |
| San Diego Jun 27–Jul 4 | $417 | $688 | $271ORD lowest, ties possible |
| New York Jun 27–Jul 4 | $307 | $569 | $262ORD lowest, ties possible |
| Harrisburg May 6–May 13 | $319 | $579 | $260ORD lowest, ties possible |
| Houston Oct 11–Oct 18 | $286 | $545 | $259ORD lowest, ties possible |
| Kansas City Jul 23–Jul 30 | $399 | $654 | $255ORD lowest, ties possible |
| Norfolk Jun 27–Jul 4 | $413 | $666 | $253ORD lowest, ties possible |
| Oklahoma City Jun 27–Jul 4 | $463 | $710 | $247ORD lowest, ties possible |
| Boston Jun 27–Jul 4 | $315 | $556 | $241ORD lowest, ties possible |
| Miami Jun 27–Jul 4 | $302 | $540 | $238ORD lowest, ties possible |
| Richmond Jun 27–Jul 4 | $439 | $669 | $230ORD lowest, ties possible |
| Wichita Jul 23–Jul 30 | $399 | $622 | $223ORD lowest, ties possible |
| Omaha Jul 23–Jul 30 | $387 | $609 | $222ORD lowest, ties possible |
| Calgary Jul 23–Jul 30 | $360 | $579 | $219ORD lowest, ties possible |
| Portland, Maine Jun 27–Jul 4 | $451 | $665 | $214ORD lowest, ties possible |
| Toronto May 6–May 13 | $447 | $659 | $212ORD lowest, ties possible |
| New Orleans Jun 27–Jul 4 | $321 | $530 | $209ORD lowest, ties possible |
| Des Moines Jun 27–Jul 4 | $379 | $572 | $193ORD lowest, ties possible |
| Grand Rapids Jun 1–Jun 8 | $313 | $506 | $193ORD lowest, ties possible |
| Knoxville Jun 27–Jul 4 | $299 | $489 | $190ORD lowest, ties possible |
| San Antonio Oct 11–Oct 18 | $399 | $585 | $186ORD lowest, ties possible |
| St. Louis Jun 27–Jul 4 | $387 | $573 | $186ORD lowest, ties possible |
| Greenville Jun 27–Jul 4 | $319 | $499 | $180ORD lowest, ties possible |
| Raleigh Jun 27–Jul 4 | $387 | $562 | $175ORD lowest, ties possible |
| Austin Jun 27–Jul 4 | $361 | $530 | $169ORD lowest, ties possible |
| Philadelphia Jun 27–Jul 4 | $363 | $531 | $168ORD lowest, ties possible |
| Hartford Oct 11–Oct 18 | $405 | $571 | $166ORD lowest, ties possible |
| Minneapolis Dec 28–Jan 4 | $168 | $328 | $160ORD lowest, ties possible |
| Tulsa Jun 27–Jul 4 | $451 | $611 | $160ORD lowest, ties possible |
| Bozeman Jun 27–Jul 4 | $384 | $540 | $156ORD lowest, ties possible |
| Charlotte Oct 11–Oct 18 | $332 | $486 | $154ORD lowest, ties possible |
| Washington Jun 27–Jul 4 | $399 | $544 | $145ORD lowest, ties possible |
| Orlando Jun 27–Jul 4 | $389 | $533 | $144ORD lowest, ties possible |
| Nashville Mar 15–Mar 22 | $287 | $428 | $141ORD lowest, ties possible |
| Portland, Oregon Oct 11–Oct 18 | $418 | $554 | $136ORD lowest, ties possible |
| Cleveland Oct 11–Oct 18 | $314 | $449 | $135ORD lowest, ties possible |
| Pittsburgh Oct 11–Oct 18 | $375 | $509 | $134ORD lowest, ties possible |
| Albuquerque Jun 27–Jul 4 | $521 | $650 | $129ORD lowest, ties possible |
| Buffalo Oct 11–Oct 18 | $366 | $495 | $129ORD lowest, ties possible |
| Cincinnati Oct 11–Oct 18 | $306 | $432 | $126ORD lowest, ties possible |
| Dallas Jun 27–Jul 4 | $447 | $573 | $126ORD lowest, ties possible |
| Fort Myers Jun 27–Jul 4 | $407 | $533 | $126ORD lowest, ties possible |
| Louisville Jun 27–Jul 4 | $365 | $479 | $114ORD lowest, ties possible |
| Albany Oct 11–Oct 18 | $456 | $567 | $111ORD lowest, ties possible |
| Tampa Jun 27–Jul 4 | $347 | $455 | $108ORD lowest, ties possible |
| Charleston Oct 11–Oct 18 | $458 | $563 | $105ORD lowest, ties possible |
| Las Vegas Dec 28–Jan 4 | $272 | $376 | $104ORD lowest, ties possible |
| Memphis Oct 11–Oct 18 | $332 | $421 | $89ORD lowest, ties possible |
| Tucson Jun 27–Jul 4 | $521 | $610 | $89ORD lowest, ties possible |
| Columbus Jun 1–Jun 8 | $347 | $434 | $87ORD lowest, ties possible |
| Los Angeles Jun 27–Jul 4 | $379 | $461 | $82ORD lowest, ties possible |
| Indianapolis Jun 1–Jun 8 | $359 | $439 | $80ORD lowest, ties possible |
| Jacksonville Dec 2–Dec 9 | $257 | $337 | $80ORD lowest, ties possible |
| San Francisco Jan 23–Jan 30 | $261 | $337 | $76ORD lowest, ties possible |
| Atlanta Oct 11–Oct 18 | $290 | $353 | $63ORD lowest, ties possible |
| Detroit Oct 11–Oct 18 | $379 | $442 | $63ORD lowest, ties possible |
| Savannah Jan 23–Jan 30 | $301 | $357 | $56ORD lowest, ties possible |
| Rochester Feb 18–Feb 25 | $277 | $319 | $42ORD lowest, ties possible |
| Birmingham Oct 11–Oct 18 | $468 | $509 | $41ORD lowest, ties possible |
| Sarasota Oct 11–Oct 18 | $540 | $507 | $33MDW lowest, ties possible |
Lowest search-result price per airport. Stops and airlines may differ. These are fare observations, not confirmed inventory or guaranteed savings. Sampling is demand-led and is not statistically representative of every flight from Chicago.
Add the journey from your address to the flight price. CTA guidance checked September 27, 2026; check current service before traveling.
The CTA Blue Line connects O’Hare with downtown Chicago and runs 24 hours. Allow for the walk or airport transfer to your terminal as well as the train ride. Check the terminal and service alerts before choosing an early departure.
CTA airport train guide ↗The CTA Orange Line connects Midway with the downtown Loop. It does not run overnight, so check the timetable for very early departures or late arrivals. Compare a realistic ground journey in both directions before choosing a fare.
CTA Midway connection guide ↗