Chicago, United States: trips from $225
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Trips to Chicago from every city
Cheapest first, per person, round trip, taxes and fees included.
$397 $225 per person, round trip, taxes and fees included You save $172 (43%)
the highest fare we saw for these dates
$295 $270 per person, round trip, taxes and fees included You save $25 (8%)
the typical fare on this route
$316 $288 per person, round trip, taxes and fees included You save $28 (9%)
the typical fare on this route
$297 per person, round trip, taxes and fees included
$348 per person, round trip, taxes and fees included
$381 $352 per person, round trip, taxes and fees included You save $29 (8%)
the typical fare on this route
$354 per person, round trip, taxes and fees included
$363 per person, round trip, taxes and fees included
$706 $413 per person, round trip, taxes and fees included You save $293 (42%)
the highest fare we saw for these dates
$420 per person, round trip, taxes and fees included
$430 per person, round trip, taxes and fees included
$498 $470 per person, round trip, taxes and fees included You save $28 (6%)
the typical fare on this route
$669 $470 per person, round trip, taxes and fees included You save $199 (30%)
the highest fare we saw for these dates
$571 $489 per person, round trip, taxes and fees included You save $82 (14%)
the typical fare on this route
$602 $520 per person, round trip, taxes and fees included You save $82 (14%)
the typical fare on this route
$772 $546 per person, round trip, taxes and fees included You save $226 (29%)
the typical fare on this route
$690 $553 per person, round trip, taxes and fees included You save $137 (20%)
the typical fare on this route
Lowest fares to Chicago by city, last 30 days
| From | Lowest, 30 days | Checks |
|---|---|---|
| Fort Lauderdale | $223 | 6 |
| Orlando | $270 | 6 |
| Philadelphia | $284 | 7 |
| Las Vegas | $288 | 6 |
| Dallas-Fort Worth | $333 | 6 |
| Denver | $337 | 2 |
| New York | $337 | 8 |
| Nashville | $342 | 5 |
| Baltimore | $345 | 1 |
| Miami | $350 | 6 |
| Tampa | $352 | 6 |
| Atlanta | $354 | 1 |
| Washington, DC | $354 | 8 |
| New Orleans | $362 | 7 |
| Syracuse | $362 | 5 |
| Austin | $381 | 1 |
| Raleigh-Durham | $388 | 6 |
| Charlotte | $391 | 2 |
| Minneapolis | $397 | 2 |
| Houston | $398 | 1 |
When to go
| Month | Season |
|---|---|
| January | avoid |
| February | avoid |
| March | avoid |
| April | fine |
| May | best |
| June | best |
| July | best |
| August | best |
| September | best |
| October | best |
| November | fine |
| December | avoid |
- June, July, August: Lakefront beaches, street festivals and Lollapalooza in early August
- November, December: Christkindlmarket and holiday lights on Michigan Avenue
December, January, February, March: Bitter cold and wind off the lake
Where to stay in Chicago
- The Loop: Architecture, theatres and Millennium Park at your doorstep.
- Magnificent Mile / Streeterville: Shopping on Michigan Avenue and lakefront hotels.
- River North: Galleries, steakhouses and the city's nightlife core.
- West Loop: Converted warehouses with the top restaurant row on Randolph Street.
- Lincoln Park: Leafy neighbourhood with a free zoo and lakefront beaches.
What to do in Chicago
- Take the Chicago Architecture Foundation river cruise
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
- Hear live blues at Kingston Mines
Good to know
| Airports | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Passport for US citizens | no |
| Price level | upscale |
| Time zone | America/Chicago |
| Kind of trip | city, culture, food, nightlife, shopping |
Chicago in pictures
Questions about Chicago
When is the best time to visit Chicago?
May, June, July, August, September and October. December, January, February, March: Bitter cold and wind off the lake
Do US citizens need a passport for Chicago?
No. Chicago is a domestic trip; a government photo ID is enough.
What is the cheapest flight to Chicago right now?
Chicago from Fort Lauderdale, Oct 23–25, 2026, from $225 per person round trip, is the cheapest trip we have published; the full list is on this page.
How expensive is Chicago on the ground?
Chicago is upscale by US standards: plan about $130 per person per day for food, getting around and tickets.