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Chicago

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Chicago Flights as Low as $166

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

Frontier Airlines
Wed, Oct 7 - Tue, Oct 27
TPA
Tampa Intl.
MDW
Midway Intl.
$166 Roundtrip, found 6 days ago
$166
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Oct 7 from Tampa Intl. to Midway Intl., returning Tue, Oct 27, priced at $166 found 6 days ago
Frontier Airlines
Sat, Sep 12 - Thu, Sep 24
TPA
Tampa Intl.
ORD
O'Hare Intl.
$166 Roundtrip, found 2 days ago
$166
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Tampa Intl. to O'Hare Intl., returning Thu, Sep 24, priced at $166 found 2 days ago
Bargain Flight
Tue, Sep 1 - Fri, Sep 4
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 5 hours ago
$216
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Tue, Sep 1 from Jacksonville Intl. to O'Hare Intl., returning Fri, Sep 4, priced at $216 found 5 hours ago
Delta
Sat, Sep 5 - Sun, Sep 6
TPA
Tampa Intl.
ORD
O'Hare Intl.
$232 Roundtrip, found 3 days ago
$232
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 5 from Tampa Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $232 found 3 days ago
Southwest Airlines
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa Intl.
MDW
Midway Intl.
$238 Roundtrip, found 5 hours ago
$238
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Tampa Intl. to Midway Intl., returning Tue, Sep 8, priced at $238 found 5 hours ago
JetBlue Airways
Sun, Sep 6 - Sun, Sep 20
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$239 Roundtrip, found 5 hours ago
$239
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sun, Sep 6 from Jacksonville Intl. to O'Hare Intl., returning Sun, Sep 20, priced at $239 found 5 hours ago
Southwest Airlines
Sun, Sep 6 - Sat, Sep 26
JAX
Jacksonville Intl.
MDW
Midway Intl.
$242 Roundtrip, found 5 hours ago
$242
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sun, Sep 6 from Jacksonville Intl. to Midway Intl., returning Sat, Sep 26, priced at $242 found 5 hours ago
American Airlines
Sun, Sep 6 - Sun, Sep 20
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$242 Roundtrip, found 5 hours ago
$242
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sun, Sep 6 from Jacksonville Intl. to O'Hare Intl., returning Sun, Sep 20, priced at $242 found 5 hours ago
American Airlines
Wed, Aug 26 - Mon, Aug 31
TPA
Tampa Intl.
RFD
Greater Rockford
$458 Roundtrip, found 5 hours ago
$458
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Aug 26 from Tampa Intl. to Greater Rockford, returning Mon, Aug 31, priced at $458 found 5 hours ago
Icelandair
Tue, Sep 1 - Mon, Sep 21
VCE
Marco Polo
ORD
O'Hare Intl.
$568 Roundtrip, found 4 days ago
$568
Roundtrip
found 4 days ago
Select Icelandair flight, departing Tue, Sep 1 from Marco Polo to O'Hare Intl., returning Mon, Sep 21, priced at $568 found 4 days ago
ITA Airways
Tue, Sep 22 - Fri, Oct 9
VCE
Marco Polo
ORD
O'Hare Intl.
$626 Roundtrip, found 4 days ago
$626
Roundtrip
found 4 days ago
Select ITA Airways flight, departing Tue, Sep 22 from Marco Polo to O'Hare Intl., returning Fri, Oct 9, priced at $626 found 4 days ago
Turkish Airlines
Tue, Sep 22 - Sat, Oct 10
VCE
Marco Polo
ORD
O'Hare Intl.
$760 Roundtrip, found 4 days ago
$760
Roundtrip
found 4 days ago
Select Turkish Airlines flight, departing Tue, Sep 22 from Marco Polo to O'Hare Intl., returning Sat, Oct 10, priced at $760 found 4 days ago
TAP Portugal
Fri, Oct 2 - Sat, Oct 17
VCE
Marco Polo
ORD
O'Hare Intl.
$798 Roundtrip, found 5 hours ago
$798
Roundtrip
found 5 hours ago
Select TAP Portugal flight, departing Fri, Oct 2 from Marco Polo to O'Hare Intl., returning Sat, Oct 17, priced at $798 found 5 hours ago
Condor
Thu, Aug 13 - Sat, Aug 22
VCE
Marco Polo
MDW
Midway Intl.
$1,049 Roundtrip, found 19 hours ago
$1,049
Roundtrip
found 19 hours ago
Select Condor flight, departing Thu, Aug 13 from Marco Polo to Midway Intl., returning Sat, Aug 22, priced at $1,049 found 19 hours ago
TAP Portugal
Fri, Oct 2 - Sat, Oct 17
XVY
Mestre Rail Station
ORD
O'Hare Intl.
$1,180 Roundtrip, found 5 hours ago
$1,180
Roundtrip
found 5 hours ago
Select TAP Portugal flight, departing Fri, Oct 2 from Mestre Rail Station to O'Hare Intl., returning Sat, Oct 17, priced at $1,180 found 5 hours ago
TAP Portugal
Fri, Oct 2 - Sat, Oct 17
XVQ
Santa Lucia Rail Station
ORD
O'Hare Intl.
$1,180 Roundtrip, found 5 hours ago
$1,180
Roundtrip
found 5 hours ago
Select TAP Portugal flight, departing Fri, Oct 2 from Santa Lucia Rail Station to O'Hare Intl., returning Sat, Oct 17, priced at $1,180 found 5 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 October, 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 15 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 $166, 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 $166 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$76

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 ...
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Congress Plaza Hotel
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 ...
8/10 Very Good! (1,961 reviews)
"I was double charged. Still trying to get resolved!!"

Reviewed on Aug 9, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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! (2,379 reviews)
"Go place to stay if your traveling and have a connection next day. Also very safe! A bit expensive especially the valet parking"

Reviewed on Aug 9, 2026

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Hilton Chicago O'Hare Airport
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
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The Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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Hyatt Regency McCormick Place 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! (2,978 reviews)
"Great"

Reviewed on Aug 9, 2026

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Hyatt Regency O'Hare Chicago
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! (1,989 reviews)
"We had a wonderful stay at the Omni Hotel! The location was absolutely perfect and made it so convenient to explore everything in the area. We loved having so many amenities right at our fingertips, and the hotel itself was beautiful, comfortable, and welcoming. The staff were incredibly friendly, ..."

Reviewed on Aug 9, 2026

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Omni Chicago Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
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Fairmont Chicago at Millennium Park
See all 5,365 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 ...
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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! (1,665 reviews)
"I loved my stay, it was great and easy to check in"

Reviewed on Aug 9, 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! (2,371 reviews)
"The staff was amazing. Never saw a unhappy face during my 7 day stay and everyone couldn't have been nicer. Property obviously well managed."

Reviewed on Aug 8, 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! (1,015 reviews)
"Toilet seat was leaking our bathroom was flooded all time bathroom fixtures are cracked and old not working properly sink tap was weird have to ask everyday to clean the room , microwave started sparking when we tried to reheat food parking ceiling was leaking some liquid made our car dirty we also ..."

Reviewed on Aug 8, 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! (2,159 reviews)
"excellent hotel near o'hare. rooms are clean and modern. appreciate the amenities....on site....several restaurants, on-site convenience shop also serving starbucks. Various meeting rooms and an ATM.... especially appreciated the round the clock shuttle to O'Hare. Service was exceptional."

Reviewed on Aug 9, 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 ...
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Carlton Inn Midway
See all 5,365 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.