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Chicago

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Chicago Flights as Low as $172

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

American Airlines
Tue, Aug 11 - Fri, Aug 14
TPA
Tampa Intl.
RFD
Greater Rockford
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Aug 11 from Tampa Intl. to Greater Rockford, returning Fri, Aug 14, priced at $172 found 4 days ago
Frontier Airlines
Mon, Nov 9 - Thu, Nov 12
TPA
Tampa Intl.
ORD
O'Hare Intl.
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 9 from Tampa Intl. to O'Hare Intl., returning Thu, Nov 12, priced at $196 found 1 day ago
American Airlines
Mon, Nov 9 - Thu, Nov 12
TPA
Tampa Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Nov 9 from Tampa Intl. to O'Hare Intl., returning Thu, Nov 12, priced at $203 found 1 day ago
JetBlue Airways
Tue, Nov 17 - Thu, Dec 3
BDL
Bradley Intl.
ORD
O'Hare Intl.
$212 Roundtrip, found 16 hours ago
$212
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Bradley Intl. to O'Hare Intl., returning Thu, Dec 3, priced at $212 found 16 hours ago
United
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa Intl.
ORD
O'Hare Intl.
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select United flight, departing Sat, Sep 5 from Tampa Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $212 found 2 days ago
Frontier Airlines
Tue, Aug 11 - Wed, Aug 12
TPA
Tampa Intl.
MDW
Midway Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Tampa Intl. to Midway Intl., returning Wed, Aug 12, priced at $215 found 1 day ago
Delta
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 5 from Tampa Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $217 found 2 days ago
Delta
Sat, Sep 5 - Sun, Sep 6
TPA
Tampa Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 5 from Tampa Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $218 found 1 day ago
United
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa Intl.
ORD
O'Hare Intl.
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select United flight, departing Sat, Sep 5 from Tampa Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $222 found 2 days ago
JetBlue Airways
Mon, Nov 2 - Wed, Nov 18
BDL
Bradley Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 16 hours ago
$224
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Mon, Nov 2 from Bradley Intl. to O'Hare Intl., returning Wed, Nov 18, priced at $224 found 16 hours ago
Delta
Tue, Aug 11 - Wed, Aug 12
TPA
Tampa Intl.
MDW
Midway Intl.
$225 Roundtrip, found 1 day ago
$225
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 11 from Tampa Intl. to Midway Intl., returning Wed, Aug 12, priced at $225 found 1 day ago
Delta
Wed, Nov 4 - Mon, Nov 16
BDL
Bradley Intl.
MDW
Midway Intl.
$297 Roundtrip, found 16 hours ago
$297
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Nov 4 from Bradley Intl. to Midway Intl., returning Mon, Nov 16, priced at $297 found 16 hours ago
American Airlines
Fri, Sep 4 - Mon, Sep 7
BDL
Bradley Intl.
RFD
Greater Rockford
$412 Roundtrip, found 16 hours ago
$412
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Bradley Intl. to Greater Rockford, returning Mon, Sep 7, priced at $412 found 16 hours ago
Delta
Tue, Aug 4 - Sat, Aug 15
BUR
Hollywood Burbank
MDW
Midway Intl.
$464 Roundtrip, found 4 days ago
$464
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 4 from Hollywood Burbank to Midway Intl., returning Sat, Aug 15, priced at $464 found 4 days ago
Frontier Airlines
Thu, Jul 30 - Thu, Aug 6
BUR
Hollywood Burbank
ORD
O'Hare Intl.
$490 Roundtrip, found 8 hours ago
$490
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Jul 30 from Hollywood Burbank to O'Hare Intl., returning Thu, Aug 6, priced at $490 found 8 hours ago
Alaska Airlines
Thu, Jul 30 - Thu, Aug 6
BUR
Hollywood Burbank
ORD
O'Hare Intl.
$502 Roundtrip, found 8 hours ago
$502
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Thu, Jul 30 from Hollywood Burbank to O'Hare Intl., returning Thu, Aug 6, priced at $502 found 8 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 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 $172, 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 $172 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

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! (2,830 reviews)
"Nice ,clean ,staff was friendly"

Reviewed on Jul 12, 2026

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Hyatt Regency O'Hare 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! (1,740 reviews)
"This place will charge you a resort fee that doubles the cost of your stay. They also won’t communicate that to you or give you any receipts. Don’t stay here."

Reviewed on Jul 12, 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! (1,914 reviews)
"Main area was nice. Hotel room was outdated"

Reviewed on Jul 13, 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! (2,350 reviews)
"$440 for a terrible room and no breakfast. I could’ve flown to Florida and had a great meal for less"

Reviewed on Jul 13, 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! (10,250 reviews)
"Walking in the staff was friendly. The room decor was very attractive, we felt right at home. The air conditioning was not working properly and so the staff offered a fan to help the air to circulate. The room service closed early, there was a miscommunication on ordering & we ended up forced to ..."

Reviewed on Jul 13, 2026

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Congress Plaza 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! (4,691 reviews)
"Great location, clean, rooftop bar and great staff."

Reviewed on Jul 13, 2026

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Hotel Riu Plaza 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! (5,348 reviews)
"The location was excellent. Thank you."

Reviewed on Jul 13, 2026

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River Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,452 reviews)
"Clean room ."

Reviewed on Jul 13, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
See all 5,263 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! (1,790 reviews)
"Room needs renovation"

Reviewed on Jul 13, 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! (1,582 reviews)
"Brief stay this time around, normally stay here whenever I come back home to the Chicagoland area, staff great as usual, recommend staying here…."

Reviewed on Jul 13, 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! (2,361 reviews)
"Room clean and stocked with necessities, staff was friendly with each interaction. No complaints for this property."

Reviewed on Jul 12, 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! (1,009 reviews)
"Wonderfully comfy bed. Decent food at the bar/restaurant. Shuttle TO/FROM airport terminal runs only every 45 minutes but takes only 15 -20 minutes so plan accordingly."

Reviewed on Jul 13, 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! (2,128 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 (1,014 reviews)
"The breakfast was really good, and parking was made very easy. Our room wasn’t cleaned or replaced with new towels our whole stay."

Reviewed on Jul 12, 2026

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Carlton Inn Midway
See all 5,263 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.