$32 Cheap flight deals from Brainerd (MSP) to Chicago (CHI)

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This Weekend's Flight Deals from Brainerd to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Sep 21 - Fri, Sep 26
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Sep 21 from Minneapolis - St. Paul Intl. to Midway Intl., returning Fri, Sep 26, priced at $168 found 2 days ago
Sun, Sep 21 - Thu, Sep 25
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$290 Roundtrip, found 3 hours ago
$290
Roundtrip
found 3 hours ago
Select Sun Country Airlines flight, departing Sun, Sep 21 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, Sep 25, priced at $290 found 3 hours ago
Fri, Sep 19 - Thu, Sep 25
BRD
Brainerd Lakes Regional
ORD
O'Hare Intl.
$478 Roundtrip, found 1 day ago
$478
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 19 from Brainerd Lakes Regional to O'Hare Intl., returning Thu, Sep 25, priced at $478 found 1 day ago

Airfares from $32 One Way, $75 Round Trip from Brainerd to Chicago

Prices starting at $75 for return flights and $32 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Dec 31 - Mon, Jan 5
MSP
Minneapolis
ORD
Chicago
$75 Roundtrip, found 6 days ago
$75
Roundtrip
found 6 days ago
Select Sun Country Airlines flight, departing Wed, Dec 31 from Minneapolis to Chicago, returning Mon, Jan 5, priced at $75 found 6 days ago
Thu, Nov 20 - Sat, Nov 22
MSP
Minneapolis
MDW
Chicago
$97 Roundtrip, found 4 hours ago
$97
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Nov 20 from Minneapolis to Chicago, returning Sat, Nov 22, priced at $97 found 4 hours ago
Tue, Nov 18 - Thu, Nov 20
MSP
Minneapolis
ORD
Chicago
$97 Roundtrip, found 20 hours ago
$97
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Nov 18 from Minneapolis to Chicago, returning Thu, Nov 20, priced at $97 found 20 hours ago
Mon, Oct 13 - Tue, Oct 14
MSP
Minneapolis
ORD
Chicago
$99 Roundtrip, found 12 hours ago
$99
Roundtrip
found 12 hours ago
Select United flight, departing Mon, Oct 13 from Minneapolis to Chicago, returning Tue, Oct 14, priced at $99 found 12 hours ago
Mon, Oct 13 - Tue, Oct 14
MSP
Minneapolis
ORD
Chicago
$99 Roundtrip, found 12 hours ago
$99
Roundtrip
found 12 hours ago
Select Delta flight, departing Mon, Oct 13 from Minneapolis to Chicago, returning Tue, Oct 14, priced at $99 found 12 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,373 reviews)

Nov 2 - Nov 4

2 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Minneapolis (MSP)

Southwest Airlines • Coach
Save 100% on your flight
Price was $437, price is now $313 per person
$313
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,714 reviews)

Oct 16 - Oct 19

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Sun Country Airlines • Coach

Chicago (ORD) to Minneapolis (MSP)

United • Coach
Save 100% on your flight
Price was $1,500, price is now $1,046 per person
$1,046
per person
found 1 day ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.

Reviewed on Sep 14, 2025

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (1,912 reviews)

Nov 2 - Nov 4

2 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Minneapolis (MSP)

Southwest Airlines • Coach
Save 100% on your flight
Price was $466, price is now $339 per person
$339
per person
found 1 day ago
The only restaurant was over priced, waiter was not pleasant, although there were few people there. When we left the room for the day, cleaning women ask if we needed anything, as to say she didn’t plan on doing anything to our room. We did ask for clean towels, and she brought them. For what we paid for this room, we expected much more

Reviewed on Aug 22, 2025

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More About Flying To Chicago from Brainerd

Route Information for Flights from Brainerd to Chicago

Origin Airport IATA Code
MSP
Destination Airport IATA Code
CHI
Distance
333 mi
Direct Flight Airlines
JAL, Delta Air Lines, Swiss, Air New Zealand, United Airlines, Qantas, SAS, Iberia, Korean Air, Brussels Airlines, Malaysia Airlines, WestJet, Gulf Air, American Airlines, KLM, Qatar Airways, Air Canada, Aer Lingus, Emirates, Copa Airlines, Aeromexico, Alaska Airlines, Avianca, Cathay Pacific, Turkish Airlines, Royal Jordanian, ANA, Lufthansa, Virgin Atlantic, British Airways
Earliest Flight Arrival
12:15PM UTC
Latest Flight Arrival
2:21AM UTC

Brainerd to Chicago

Whether you want to book cheap flights from Brainerd to Chicago or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Brainerd to Chicago flights.

Make the Most of Your Vacation

Not only does Orbitz have cheap deals for Brainerd to Chicago flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Chicago.

Planning on the Go

Book your flights from Brainerd to Chicago wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Brainerd to Chicago flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

Craft Your Perfect Vacation

Orbitz takes the stress out of vacation planning with great deals on flights from Brainerd to Chicago, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.

Keep Informed With Orbitz

With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Brainerd to Chicago flights. The alerts can be sent straight to your mobile phone or email.

Frequently asked questions

Are there non-stop flights from Brainerd to Chicago?
Nonstop flights are offered by no less than 4 airlines from Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to O'Hare Airport, so you could be booking your fun-filled vacation within minutes. Here are some sought-after carriers to check out:

  • Delta
  • United Airlines
  • American Airlines
  • Sun Country Airlines

What is the shortest flight from Brainerd to Chicago?
It can take just 1 hour and 23 minutes to get from MSP to O'Hare Airport. Buckle up and enjoy the ride, because you'll be landing in a heartbeat.
What airlines fly from Brainerd to Chicago most frequently?
These are the carriers with frequent flights from MSP to ORD. Reserve a seat with one of the following and discover why they are the most sought after: Delta - (DL) with 204 flights every month United Airlines - (UA) with 199 flights every month American Airlines - (AA) with 143 flights every month Sun Country Airlines - (SY) with 17 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.