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Chicago

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Chicago Flights as Low as $40

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

Frontier Airlines
Thu, Nov 19 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$40 Roundtrip, found 11 hours ago
$40
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 5, priced at $40 found 11 hours ago
Frontier Airlines
Sat, Oct 31 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$54 Roundtrip, found 5 hours ago
$54
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Oct 31 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Nov 14, priced at $54 found 5 hours ago
Frontier Airlines
Mon, Dec 7 - Thu, Dec 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 18 hours ago
$58
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Dec 10, priced at $58 found 18 hours ago
Frontier Airlines
Sun, Dec 6 - Wed, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$64 Roundtrip, found 18 hours ago
$64
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sun, Dec 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Dec 9, priced at $64 found 18 hours ago
Delta
Thu, Nov 19 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 11 hours ago
$163
Roundtrip
found 11 hours ago
Select Delta flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 5, priced at $163 found 11 hours ago
Southwest Airlines
Sat, Oct 31 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$163 Roundtrip, found 5 hours ago
$163
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Oct 31 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Nov 14, priced at $163 found 5 hours ago
United
Wed, Nov 11 - Wed, Nov 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 12 hours ago
$163
Roundtrip
found 12 hours ago
Select United flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $163 found 12 hours ago
American Airlines
Thu, Nov 19 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 11 hours ago
$163
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 5, priced at $163 found 11 hours ago
American Airlines
Wed, Oct 28 - Tue, Nov 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Oct 28 from Los Angeles Intl. to O'Hare Intl., returning Tue, Nov 3, priced at $177 found 4 hours ago
Southwest Airlines
Thu, Nov 26 - Wed, Dec 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$187 Roundtrip, found 4 hours ago
$187
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Nov 26 from Los Angeles Intl. to Midway Intl., returning Wed, Dec 9, priced at $187 found 4 hours ago
Alaska Airlines
Wed, Oct 28 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 13 hours ago
$197
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Wed, Oct 28 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 7, priced at $197 found 13 hours ago
Delta
Tue, Jan 12 - Sat, Jan 30
SRQ
Sarasota-Bradenton Intl.
MDW
Midway Intl.
$265 Roundtrip, found 20 hours ago
$265
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Jan 12 from Sarasota-Bradenton Intl. to Midway Intl., returning Sat, Jan 30, priced at $265 found 20 hours ago
Delta
Tue, Nov 3 - Tue, Nov 17
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$265 Roundtrip, found 20 hours ago
$265
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Nov 3 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $265 found 20 hours ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$281 Roundtrip, found 15 hours ago
$281
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $281 found 15 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Dec 20 - Sat, Dec 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$459 Roundtrip, found 16 hours ago
$459
Roundtrip
found 16 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Dec 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 26, priced at $459 found 16 hours ago
Sun Country Airlines
Wed, Nov 25 - Sat, Nov 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$793 Roundtrip, found 16 hours ago
$793
Roundtrip
found 16 hours ago
Select Sun Country Airlines flight, departing Wed, Nov 25 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 28, priced at $793 found 16 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 November, 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 $40, 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 $40 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$40

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! (10,212 reviews)
"When I first walked in to the hotel, I was impressed by the beautiful lobby. But that was it. The rooms are extremely dated, the bathtub has rust all over, and the door frames have huge dents. Yes, they do have nice high ceilings, but the furniture needs to be updated, and the windows need room darkening ..."

Reviewed on Oct 7, 2026

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Congress Plaza Hotel
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! (5,483 reviews)
"Clean and very helpful staff. Great location!"

Reviewed on Oct 7, 2026

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River 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! (2,429 reviews)
"N/A"

Reviewed on Oct 7, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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 ...
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The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
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Hilton Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
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Eurostars Magnificent Mile
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
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The Wade
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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Hyatt Regency Chicago
See all 5,442 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 ...
7.4/10 Good! (2,006 reviews)
"I felt very safe! The shuttle tends to arrive a bit late but overall good."

Reviewed on Oct 7, 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! (1,819 reviews)
"The hotel was super clean and spacious. So many amenities that were useful. Staff was a delight and super welcoming. Would totally recommend and stay again!"

Reviewed on Oct 6, 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 ...
9.4/10 Exceptional! (2,393 reviews)
"Staff were amazing, clean room, great breakfast. Good people who cared."

Reviewed on Oct 6, 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 ...
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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! (2,265 reviews)
"Very clean, friendly staff we liked the walking distance to Rosemont theatre and to the mall"

Reviewed on Oct 5, 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 ...
5.8/10 (1,001 reviews)
"furniture layout a little awkward, ate dinner on the bed. They ran out of knives for breakfast and didn't seem bothered by it. Jewel is 1 mile away and they could have bought more. Breakfast was fine. Room could use a little TLC, paint. Putting shampoo by the sink wasn't helpful, no soap. Fridge, ..."

Reviewed on Oct 6, 2026

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Carlton Inn Midway
See all 5,442 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.