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Chicago

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Chicago Flights as Low as $128

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

Frontier Airlines
Tue, Aug 25 - Wed, Sep 9
MCO
Orlando Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Orlando Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $128 found 2 days ago
Frontier Airlines
Wed, Aug 26 - Tue, Sep 1
MCO
Orlando Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 14 hours ago
$138
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $138 found 14 hours ago
Frontier Airlines
Tue, Jul 21 - Sat, Jul 25
MCO
Orlando Intl.
ORD
O'Hare Intl.
$142 Roundtrip, found 14 hours ago
$142
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Orlando Intl. to O'Hare Intl., returning Sat, Jul 25, priced at $142 found 14 hours ago
Frontier Airlines
Wed, Aug 26 - Thu, Aug 27
MCO
Orlando Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 14 hours ago
$153
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Orlando Intl. to O'Hare Intl., returning Thu, Aug 27, priced at $153 found 14 hours ago
Frontier Airlines
Tue, Jul 21 - Thu, Aug 6
MCO
Orlando Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 14 hours ago
$157
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Orlando Intl. to O'Hare Intl., returning Thu, Aug 6, priced at $157 found 14 hours ago
Frontier Airlines
Mon, Aug 17 - Thu, Aug 20
MCO
Orlando Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 6 days ago
$163
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Aug 17 from Orlando Intl. to O'Hare Intl., returning Thu, Aug 20, priced at $163 found 6 days ago
Bargain Flight
Fri, Oct 23 - Mon, Oct 26
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$186 Roundtrip, found 5 days ago
$186
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Fri, Oct 23 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $186 found 5 days ago
Bargain Flight
Fri, Oct 23 - Mon, Oct 26
GSP
Greenville-Spartanburg Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 5 hours ago
$189
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Fri, Oct 23 from Greenville-Spartanburg Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $189 found 5 hours ago
American Airlines
Tue, Aug 25 - Wed, Sep 9
MCO
Orlando Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 25 from Orlando Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $217 found 2 days ago
Frontier Airlines
Wed, Aug 26 - Wed, Sep 2
MCO
Orlando Intl.
MDW
Midway Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Midway Intl., returning Wed, Sep 2, priced at $220 found 1 day ago
Delta
Sat, Oct 3 - Sat, Oct 3
MCO
Orlando Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 3 from Orlando Intl. to O'Hare Intl., returning Sat, Oct 3, priced at $237 found 1 day ago
Frontier Airlines
Sat, Aug 1 - Thu, Aug 20
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$256 Roundtrip, found 23 hours ago
$256
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Aug 1 from Charlotte-Douglas Intl. to Midway Intl., returning Thu, Aug 20, priced at $256 found 23 hours ago
JetBlue Airways
Tue, Aug 25 - Wed, Sep 9
MCO
Orlando Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Orlando Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $277 found 2 days ago
Delta
Sat, Aug 8 - Mon, Aug 24
GSP
Greenville-Spartanburg Intl.
MDW
Midway Intl.
$289 Roundtrip, found 23 hours ago
$289
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Aug 8 from Greenville-Spartanburg Intl. to Midway Intl., returning Mon, Aug 24, priced at $289 found 23 hours ago
American Airlines
Fri, Aug 28 - Sun, Aug 30
MCO
Orlando Intl.
RFD
Greater Rockford
$338 Roundtrip, found 1 day ago
$338
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 28 from Orlando Intl. to Greater Rockford, returning Sun, Aug 30, priced at $338 found 1 day ago
Sun Country Airlines
Fri, Nov 13 - Sun, Nov 15
MCO
Orlando Intl.
ORD
O'Hare Intl.
$363 Roundtrip, found 3 days ago
$363
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Fri, Nov 13 from Orlando Intl. to O'Hare Intl., returning Sun, Nov 15, priced at $363 found 3 days 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 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 $128, 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 $128 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$138

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! (10,135 reviews)
"The Congress was my number #1 place for 30 years. It's an older hotel and shows. Doors in my suite don't close or lock correctly. The room wasn't cleaned when requested so my travel mate could make bets if the room was serviced or not by the time we returned. Not even when I called House keeping. ..."

Reviewed on Jun 27, 2026

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Congress Plaza 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! (2,319 reviews)
"Staffs were ridiculous. Never thought I would hear that “he works for tips not free”. I paid $500 including tax and this is what I was told. And daughter got bit by I don’t know what all over her body. I don’t know how all of the treatments they think was okay to a customer. We didn’t ask for much ..."

Reviewed on Jun 27, 2026

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Hilton Chicago O'Hare Airport
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! (1,828 reviews)
"Best location on Michigan Avenue"

Reviewed on Jun 27, 2026

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Omni Chicago 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! (2,735 reviews)
"This place was very busy but they managed to keep it clean. Friendly and helpful staff."

Reviewed on Jun 27, 2026

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Hyatt Regency O'Hare 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! (4,466 reviews)
"Loved our stay! Staff was friendly. The food downstairs was delicious!!! Only one minor hiccup, we found a pair of shorts and men’s underwear in our room when we checked in. I just threw them out. Mistakes happen but overall we enjoyed our stay in Chicago"

Reviewed on Jun 27, 2026

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Hilton Chicago/Magnificent Mile Suites
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! (4,553 reviews)
"Clean room, friendly staff, great location and a nice roof top and lobby bar"

Reviewed on Jun 27, 2026

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Hotel Riu Plaza 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! (1,650 reviews)
"Checking in was a breeze. Staff was very friendly and helpful. Love the complimentary gifts, drink and dinner coupons. What made it even better the area."

Reviewed on Jun 27, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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! (5,263 reviews)
"Staff was excellent. Elevators got congested the higher the floor you stay on."

Reviewed on Jun 27, 2026

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River Hotel
See all 5,355 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! (1,745 reviews)
"The room smelled and was a bit clammy. The carpet seemed a bit sticky. It was ok and got the job done."

Reviewed on Jun 26, 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! (1,540 reviews)
":)"

Reviewed on Jun 27, 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! (2,348 reviews)
"The hotel was very well kept and clean. The daily breakfast was perfect."

Reviewed on Jun 26, 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! (1,002 reviews)
"Staff was very helpful, enjoyed the stay and the breakfast. Parking was free and there is a parking deck (upper and lower) behind the hotel."

Reviewed on Jun 23, 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! (2,094 reviews)
"Close to the airport and in walking distance to the tram. Food on property was just ok"

Reviewed on Jun 26, 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 (1,004 reviews)
"I stayed one night before an early morning flight out of Midway. While I checked in properly and received my room key, something happened in their system and the room appeared available. As a result, I was awoken by someone trying to get into my room at 12:30 am, who I shouted at and they went away. ..."

Reviewed on Jun 26, 2026

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Carlton Inn Midway
See all 5,355 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.