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Chicago

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Chicago Flights as Low as $108

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $108 found 1 day ago
Frontier Airlines
Tue, Sep 22 - Tue, Oct 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $108 found 3 days ago
Bargain Flight
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$175 Roundtrip, found 15 hours ago
$175
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $175 found 15 hours ago
Delta
Wed, Sep 30 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 30, priced at $192 found 4 days ago
American Airlines
Tue, Sep 22 - Tue, Oct 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $197 found 3 days ago
Frontier Airlines
Wed, Aug 12 - Tue, Aug 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$211 Roundtrip, found 3 days ago
$211
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Los Angeles Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $211 found 3 days ago
Bargain Flight
Sat, Aug 22 - Mon, Aug 24
PNS
Pensacola Intl.
ORD
O'Hare Intl.
$225 Roundtrip, found 2 days ago
$225
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Aug 22 from Pensacola Intl. to O'Hare Intl., returning Mon, Aug 24, priced at $225 found 2 days ago
Frontier Airlines
Tue, Aug 18 - Sat, Sep 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$246 Roundtrip, found 23 hours ago
$246
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to Midway Intl., returning Sat, Sep 12, priced at $246 found 23 hours ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$256 Roundtrip, found 12 hours ago
$256
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $256 found 12 hours ago
Delta
Sun, Sep 6 - Tue, Sep 22
MOB
Mobile Regional
ORD
O'Hare Intl.
$303 Roundtrip, found 6 days ago
$303
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Sep 6 from Mobile Regional to O'Hare Intl., returning Tue, Sep 22, priced at $303 found 6 days ago
Delta
Tue, Sep 29 - Sat, Oct 3
MOB
Mobile Regional
MDW
Midway Intl.
$307 Roundtrip, found 23 hours ago
$307
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Sep 29 from Mobile Regional to Midway Intl., returning Sat, Oct 3, priced at $307 found 23 hours ago
Alaska Airlines
Tue, Oct 13 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$315 Roundtrip, found 22 hours ago
$315
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Tue, Oct 13 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 17, priced at $315 found 22 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$332 Roundtrip, found 3 days ago
$332
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $332 found 3 days ago
JetBlue Airways
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$337 Roundtrip, found 1 day ago
$337
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $337 found 1 day ago
Delta
Wed, Aug 19 - Tue, Sep 8
PNS
Pensacola Intl.
MDW
Midway Intl.
$355 Roundtrip, found 3 days ago
$355
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 19 from Pensacola Intl. to Midway Intl., returning Tue, Sep 8, priced at $355 found 3 days ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$373 Roundtrip, found 15 hours ago
$373
Roundtrip
found 15 hours ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $373 found 15 hours ago

Cheap Flights to Chicago

Fall in love at first flight with your vacation to Chicago by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chicago on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chicago, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chicago

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chicago with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Chicago?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chicago are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chicago?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Chicago.

What airport is best to fly into Chicago?

When you’re planning your trip to Chicago, convenience is the name of the game. Luckily, Chicago Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Chicago must-do list.

How much are flights to Chicago?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chicago on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $108, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chicago?

The trick to saving a stack of cash on your flight to Chicago? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $108 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$108

Last Minute Hotel Deals in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,140 reviews)
"Complicated"

Reviewed on Jun 19, 2026

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Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,681 reviews)
"The only thing that would have made it excellent was if they had a pool/spa."

Reviewed on Jun 20, 2026

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Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,601 reviews)
"Our stay was amazing! Staff was very helpful!"

Reviewed on Jun 19, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,309 reviews)
"It was a great hotel for staying on site"

Reviewed on Jun 19, 2026

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Hilton Chicago O'Hare Airport
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,620 reviews)
"If I'd spent all my time in the lobby, I might have felt like I was staying at the Ambassador. As for the room where I actually stayed, it wasn't much better than the average roadside motel room of my childhood. The original Ambassador has suffered death by a thousand cuts. The location, of course, ..."

Reviewed on Jun 20, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,449 reviews)
"Clean room exelent"

Reviewed on Jun 19, 2026

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Hilton Chicago/Magnificent Mile Suites
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
8.6/10 Excellent! (3,017 reviews)
"Clean room, helpful staff, the room was a lot larger than I anticipated. Also, the hotel was conveniently located to everything that I planned during my stay which was a plus!"

Reviewed on Jun 19, 2026

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Warwick Allerton - Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.6/10 Good! (2,619 reviews)
"The staff was helpful and friendly. I liked that there was two different restaurants you could eat at within the hotel (not super expensive). It’s close within walking distance of sightseeing, transportation and a ton of other local food places. The hotel rooms do need to updated. The carpets are ..."

Reviewed on Jun 20, 2026

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Travelodge by Wyndham Downtown Chicago
See all 5,560 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Hotels With Free Airport Shuttle

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

3.5 out of 5
2951 Touhy Ave Elk Grove Village IL
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7.6/10 Good! (1,718 reviews)
"Clean, quiet, safe place to stay in the O’Hare airport area with free airport shuttle."

Reviewed on Jun 20, 2026

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Super 8 by Wyndham Chicago O'Hare Airport
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue Bensenville IL
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (1,510 reviews)
"good place to stay!! good breakfast selection"

Reviewed on Jun 18, 2026

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Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

2.5 out of 5
3939 N Mannheim Rd Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,344 reviews)
"Nice rooms. Good breakfast. Good staff."

Reviewed on Jun 20, 2026

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Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
5615 North Cumberland Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.2/10 Very Good! (1,004 reviews)
"Everything was excellent, starting with the front desk, thank you"

Reviewed on Jun 18, 2026

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Holiday Inn Chicago O'Hare Area by IHG
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

4.5 out of 5
5300 N River Rd Rosemont IL
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
9.4/10 Exceptional! (2,083 reviews)
"The room was very clean, bed was very comfortable. This is by far the best hotel I’ve stayed in."

Reviewed on Jun 15, 2026

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Loews Chicago O'Hare Hotel
Carlton Inn Midway

Carlton Inn Midway

2 out of 5
4944 S Archer Ave Chicago IL
Book a stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (1,002 reviews)
"About the room, it’s so Dusty on the bed. Breakfast is not so much choice. No shampoo, body wash, lotion. Bathroom sink is broken. I don’t want to come back again."

Reviewed on Jun 19, 2026

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Carlton Inn Midway
See all 5,560 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.