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Chicago

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Chicago Flights as Low as $93

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

Frontier Airlines
Tue, Aug 11 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$93 Roundtrip, found 3 hours ago
$93
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $93 found 3 hours ago
Frontier Airlines
Tue, Sep 29 - Sat, Oct 10
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$95 Roundtrip, found 22 hours ago
$95
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Tue, Sep 29 from George Bush Intercontinental to O'Hare Intl., returning Sat, Oct 10, priced at $95 found 22 hours ago
Frontier Airlines
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$96 Roundtrip, found 22 hours ago
$96
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $96 found 22 hours ago
Frontier Airlines
Wed, Aug 12 - Sun, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 19 hours ago
$99
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 16, priced at $99 found 19 hours ago
Frontier Airlines
Tue, Sep 29 - Wed, Sep 30
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$100 Roundtrip, found 22 hours ago
$100
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Tue, Sep 29 from George Bush Intercontinental to O'Hare Intl., returning Wed, Sep 30, priced at $100 found 22 hours ago
United
Tue, Aug 18 - Mon, Aug 31
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$155 Roundtrip, found 22 hours ago
$155
Roundtrip
found 22 hours ago
Select United flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Aug 31, priced at $155 found 22 hours ago
Delta
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$155 Roundtrip, found 22 hours ago
$155
Roundtrip
found 22 hours ago
Select Delta flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $155 found 22 hours ago
American Airlines
Mon, Sep 14 - Thu, Sep 17
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Sep 14 from George Bush Intercontinental to O'Hare Intl., returning Thu, Sep 17, priced at $179 found 3 days ago
Delta
Tue, Sep 29 - Wed, Sep 30
IAH
George Bush Intercontinental
MDW
Midway Intl.
$199 Roundtrip, found 22 hours ago
$199
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Sep 29 from George Bush Intercontinental to Midway Intl., returning Wed, Sep 30, priced at $199 found 22 hours ago
Frontier Airlines
Tue, Aug 25 - Wed, Sep 9
SLC
Salt Lake City Intl.
ORD
O'Hare Intl.
$266 Roundtrip, found 5 days ago
$266
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Salt Lake City Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $266 found 5 days ago
JetBlue Airways
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $297 found 2 days ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$372 Roundtrip, found 1 day ago
$372
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $372 found 1 day ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$392 Roundtrip, found 3 hours ago
$392
Roundtrip
found 3 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 $392 found 3 hours ago
Alaska Airlines
Fri, Sep 4 - Tue, Sep 8
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$775 Roundtrip, found 5 hours ago
$775
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Fri, Sep 4 from George Bush Intercontinental to O'Hare Intl., returning Tue, Sep 8, priced at $775 found 5 hours ago
American Airlines
Mon, Jul 20 - Wed, Jul 22
IAH
George Bush Intercontinental
RFD
Greater Rockford
$826 Roundtrip, found 2 hours ago
$826
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, Jul 20 from George Bush Intercontinental to Greater Rockford, returning Wed, Jul 22, priced at $826 found 2 hours ago
Delta
Wed, Jul 15 - Wed, Jul 15
SLC
Salt Lake City Intl.
MDW
Midway Intl.
$1,185 Roundtrip, found 1 day ago
$1,185
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 15 from Salt Lake City Intl. to Midway Intl., returning Wed, Jul 15, priced at $1,185 found 1 day 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 August, 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 16 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 $93, 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 $93 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$96

Last Minute Hotel Deals in Chicago

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! (1,734 reviews)
"Surprise fees upfront when you book with third party sites like, Expedia. Expect to cough up a few hundred dollars before you even get to the elevator. Other than that it’s a gorgeous hotel with incredible surrounding areas. Not too far from the beach as well. The breakfast buffet was also ..."

Reviewed on Jul 11, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,908 reviews)
"Great location and a friendly staff made this a great experience. The rooms are very nice, but a little dated, which made it feel a little less clean. The staff was amazing, especially the doorman/bellman, Ham. He went out of his way help everytime we arrived or departed, he asked how our day was ..."

Reviewed on Jul 11, 2026

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Omni Chicago Hotel
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! (2,342 reviews)
"."

Reviewed on Jul 11, 2026

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Hilton Chicago O'Hare Airport
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! (10,229 reviews)
"Older hotel, but nice"

Reviewed on Jul 11, 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! (2,818 reviews)
"Dated but comfortable and had all amenities"

Reviewed on Jul 11, 2026

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Hyatt Regency O'Hare Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,337 reviews)
"Locatio"

Reviewed on Jul 11, 2026

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River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,678 reviews)
"There was not any microwave for reheating the food neither in the room nor in the restaurant."

Reviewed on Jul 11, 2026

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Hotel Riu Plaza Chicago
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! (4,549 reviews)
"Ok"

Reviewed on Jul 11, 2026

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Hilton Chicago/Magnificent Mile Suites
See all 5,276 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! (1,782 reviews)
"Staff, parking and airport shuttle."

Reviewed on Jul 11, 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! (1,576 reviews)
"This hotel was absolutely disgusting. We had to change rooms three times during our stay. The first room smelled absolutely horrible, and the second room had a bed that was soaking wet. We only stayed because we couldn’t get a full refund and there were no other hotels available nearby. The hotel ..."

Reviewed on Jul 11, 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! (2,357 reviews)
"We stayed here before flying out of O’Hare. The shuttle and breakfast were great! The beds were also comfortable."

Reviewed on Jul 11, 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 ...
8.4/10 Very Good! (1,007 reviews)
"Perfect place to stay for attending Cubs games without a car. Fly into O’Hare, take the free shuttle bus to the property, check in, make the short walk to the CTA train, to the Addison St bus to Wrigley."

Reviewed on Jul 10, 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! (2,127 reviews)
"We arrived at terminal 5, there is 1 pickup for the hotel on the airport, it is a journey to get there. Many hotels pick up at terminal 5, why dont they ? We weren given a room near the elevator, and the hallway noise seems to be quite prominent in the room. In addition, the room next door was a ..."

Reviewed on Jul 11, 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 (1,011 reviews)
"I think this hotel is good for you and your spouse, but not if you’re traveling with children. It’s a good option for a one- or two-night stay, especially if you just need a place to sleep."

Reviewed on Jul 9, 2026

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Carlton Inn Midway
See all 5,276 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.